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Toluene → 7-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17279
ノート
印刷プレビュー

反応式

HRID 17279 の反応式
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:20][C:21]1[C:26]([OH:27])=[C:25]([NH:28][C:29](=O)[C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([C:35]#[N:36])=[C:23]([CH3:37])[C:22]=1[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=1>O>[Br:20][C:21]1[C:22]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=2)=[C:23]([CH3:37])[C:24]([C:35]#[N:36])=[C:25]2[C:26]=1[O:27][C:29]([C:30]([CH3:32])([CH3:31])[CH3:33])=[N:28]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630804N-(2-Bromo-5-cyano-3,3'-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

生成物 1

HCID 685850047-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile収率 95%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Toluene (45 ml), p-toluenesulfonic acid monohydrate (21.0 mg, 111 μmol) were added to N-(2-bromo-5-cyano-3,3′-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-16) (446 mg, 1.11 mmol), followed by refluxing with a Dean-Stark condenser for 3 hours. After cooling, water (50 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (50 ml×2). The organic layer was washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the entitled compound (404 mg, 95%) as a colorless solid.

後処理

  1. temperatureby refluxing with a Dean-Stark condenser for 3 hours
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl acetate (50 ml×2)
  4. washThe organic layer was washed with saturated brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-0bbb1f0ef9f34865b1c08f15cf05cf63
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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